Anthraquinone dyestuffs



ANTHRAQUINONE DYESTUFFS Frank Lodge and'Henry Alfred Piggott, Blackley, Manchester, England, assignors to Imperial Chemical industries Limited, a corpora- V N .tion of Great Britain Y No Drawing: Application November 30, 1934, Serial No. 755,512. In Great Britain December 6, 1933 t v 7 Claims. (01. 260-59) According to this invention, we manufacture ofethylene glyc 10. parts of stearamide and new anthraquinone dyestuffs for acetate artificial 1 06 parts of ethylene oxide infa closed vessel-at silk by interacting a 1-aminoanthraquinone-2- 1 20'13.0- until the internal pressure'fallsto'zero,

sulphonic acid substituted in the ii-position by and extracting the unchanged tearami e i om an amino, alkylamino, anilino or toluidino group, the product with light petroleum) and 250 parts 5 with a condensation product of ethylene oxide of 32% aqueous sodium hydroxide solution are and a hydroxy compound as defined below. stirred at 100 C. for 1 hour. The reaction mass Also according to this invention, we use the s d luted with 0 parts f Wa and the dy I new dyes for dyeing and printing acetate arti- Stufi p e pi ated by acidifying With hydrochlo- 10 ficial silk on which they show'good fastness to no acid. T p ipi a e is fil r ff and 16' washing. Washed well with cold water. 7

.By a condensation. product of ethylene oxide The product When dry is violet witha bronzy and a hydroxy compound we mean monomethylreflex; it dissolves with a bluish red colour in glycol, monoethylglycol, glycol hydroxyethyl concentrated sulphuricacid andwith a violet ether, glycerol trihydroxyethyl ether or othercolour in alcohol. It may be used to dye acetate 15' compound containing the group p artificial silk in violet shades. a v

V Example 2.-100 parts of sodium-l-aminol- H anilinoanthraquinone-2-sulph0nate, 300 parts of where n isa whole number, and where two or glycerol tri(hydroxyethyl)ether (prepared by 20 more such groups maybe present. We include heating glycerolwith 3 molecular proportions'of 20 also .the highly soluble condensation products ethylene oxide in a closed pressure-resisting've'sobtained or obtainable byrlsubmitting ethylenev sel at 150 C.) and 150 parts of 32% aqueous sooxide either alone or with. a hydroxy body, to dium hydroxide solution are stirred and heated heat and/or a catalyst adapted to facilitate, or, at 100 C. for 1 hour. The dyestufi is isolated initiate condensation, such as sodium hydroxide from the reaction mass as in Example 1. or a tertiary organic base.- Typical examples ofv The dry product is violet with a bronzy reflex, it such highly soluble condensation products. are dissolves with a bluishred colour in concentrated those prepared by heating mannitol with more sulphuric acid. It may be used to dye acetate than 6 molecular proportions'of ethylene oxide, artificial silkinyiolet shades. V v

or by. condensing -.ethylene oxide with carbohy- I Emm ple' ..3.'- 'rhe polyethylene'glycol used in 3 drates such as glucose or fructose. These con- 'p l'iS repla'cediby an q l ht of the densation products are believed to have consticondensation product obtained by ea n mantutions coming within the definition given, see n t l wi h 30 molecular p p r on f hyl n for example H. Staudinger, Die Hochmolecular oxide in the presence of stearamide or an alkaline organischen Verbindugen-Kautschuk und Celcataly 35 lulose, Berlin, 1932, page 278, et seq., butw d The product is violet, it dissolves in concennot make the inclusion of them in our inventrailed Sulphuric a id With a bluish red colour tion subject to the correctness of constitution and in alcohol With a Violet C01011r- It y s acegiven, tate artificial silk in violet shades. A similar 40 In carrying the invention into practical ef- Product is Obtained by Substituting Sorbitol for 40 fect, the manufacture of the dyes may be efiected manniiol. by heating the reagents in presence of a base, tt p e -InStead of the sodium-l-aminole. g. in aqueous alkaline medium, or, alternativeanilinoanthraquinone2-sulphonate of E a pl 2 ly, the anthraquinonesulphonic acids or their there is used an equal W t of Sodium ,4-dialkali salts may be heated with an alkali metal amin anthraquinone-2-sulphonate. The prod- 4,5

derivative of the said hydroxyl compound either not is isolated as in Example 1. alone or in presence of an inert medium. The iThe filo-Obtained dyestufi When y a a dark dyes may be applied by the known proces es for red bronzy colour, and dissolves in concentrated applying aminoanthraquinones to acetate arti- Sulphuric acid with an orange 0 t dyes 5o ficial silk. acetate artificial silk in bluish red shades.

The following examples in which parts are by Exa ple 5.-Instead of the sodium 1,4-diweight illustrate but do not limit the invention. aminoanthraquinone2-sulphonate f xample 4 Example 1.-100 parts of s0dium-1-amino-4- there is used sodium l-amino-i-m'ethylaminoananilinoanthraquinone-2-sulphonate, 400 parts of thraquin0 ulph0nate. The product is isopolyethylene glycol (prepared by heating 2 parts lated in the usual way. 55

The so-obtained dyestuff is a dark substance which dyes acetate artificial silk in reddish-violet shades.

We claim:

1. Process for the manufacture of new anthraquinone dyestuffs for cellulose ester or ether materials which comprises the interaction of a compound of formula:

l co SOaH wherein R represents a member of the group consisting of hydrogen, alkyl, phenyl and tolyl in alkaline medium, with the condensation product of ethylene oxide and a polyhydric aliphatic alcohol.

2; Process for the manufacture of new anthraquinone dyestuffs for cellulose ester or ether materials which comprises the interaction of a compound of formula:

V Z I NH-R SOaH NHa wherein R represents a member of the group consisting of hydrogen, alkyl, phenyl and tolyl in alkaline medium, with the condensation product of ethylene oxide and ethylene glycol.

4. Process for the manufacture of new anthraquinone dyestuffs for cellulose ester or ether materials which comprises the interaction of a compound of formula:

CO (I S 03H wherein R represents a member of the group consisting of hydrogen, alkyl, phenyl and tolyl in alkaline medium, with the condensation product of ethylene oxide and glycerol.

5. Process for the manufacture of new anthraquinone dyestuffs for cellulose ester or ether materials which comprises the interaction of a compound of formula:

NHR

wherein R represents a member of the group consisting of hydrogen, alkyl, phenyl and tolyl in alkaline medium, with the condensation product of ethylene oxide and a compound of the sugar group.

6. A new anthraquinone dyestuif being the reaction product of a l-amino-anthraquinone-Z- sulphonic acid, carrying in position 4 a substituent chosen from the group consisting of amino, alkylamino, anilino and toluidino, and a [3-hydroxyethyl ether of an aliphatic alcohol.

7. An anthraquinone dyestuff whch is the reaction product of l-amino-4-anilino-anthraquinone-2-sodium sulfonate and glycerol tri-(hydroxy ethyl) ether which when in dry form is violet in color, dissolving in concentrated sulfuric acid with a bluish-red color, and which dyes cellulose acetate silk in violet'shades.

FRANK LODGE. HENRY ALFRED PIGGOTT. 

